HCID 46244530, compound → HCID 46833478, compound

HRID 2199606Notes

Reaction equation

HRID 2199606 reaction equation
C(N(C1C=CC=CC=1)S(C1C=CC(N2C(=O)C3CN(C(OC(C)(C)C)=O)CCC=3N2)=NC=1)(=O)=O)C.[CH:36]1([N:41]([CH2:60][CH:61]2[CH2:65][O:64]C(C)(C)[O:62]2)[S:42]([C:45]2[CH:46]=[N:47][C:48]([N:51]3[C:55](=[O:56])[C:54]4[CH2:57][S:58][CH2:59][C:53]=4[NH:52]3)=[CH:49][CH:50]=2)(=[O:44])=[O:43])[CH2:40][CH2:39][CH2:38][CH2:37]1>CC(O)=O>[CH:36]1([N:41]([CH2:60][CH:61]([OH:62])[CH2:65][OH:64])[S:42]([C:45]2[CH:46]=[N:47][C:48]([N:51]3[C:55](=[O:56])[C:54]4[CH2:57][S:58][CH2:59][C:53]=4[NH:52]3)=[CH:49][CH:50]=2)(=[O:43])=[O:44])[CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 46244530HCID 46244530, compoundHCID 67455858HCID 67455858, compound

Product 1

HCID 46833478HCID 46833478, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 470 mg (0.54 mmol) of 6 N-cyclopentyl-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-6-(3-oxo-4,6-dihydro-1H-thieno[3,4-c]pyrazol-2(3H)-yl)pyridine-3-sulfonamide in 1 mL of AcOH is heated at 80° C. for 4 hours. The medium is concentrated under reduced pressure and then purified by reverse-phase chromatography on a C18 column, eluting with a 10−3N HCl/CH3CN gradient of from 0 to 100% CH3CN. 48 mg of N-cyclopentyl-N-(2,3-dihydroxypropyl)-6-(3-oxo-4,6-dihydro-1H-thieno[3,4-c]pyrazol-2(3H)-yl)pyridine-3-sulfonamide are obtained in the form of a white solid.

Workup

  1. concentrationThe medium is concentrated under reduced pressure
  2. custompurified by reverse-phase chromatography on a C18 column
  3. washeluting with a 10−3N HCl/CH3CN gradient of from 0 to 100% CH3CN

Sources & evidence

ORD record
ord-ba4db6f6197d4db381be3feb5e797ee2
Source dataset
uspto-grants-2016_06
Patent number
US09359329B2

Reaction notes

Loading…